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Ring transformations in reactions of heterocyclic compounds with nucleophiles (XX) . Conversion of 5‐nitropyrimidine into 3,5‐dinitropyridine. A novel ring transformation
Author(s) -
van der Plas H. C.,
Jongejan H.,
Koudijs A.
Publication year - 1978
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570150323
Subject(s) - chemistry , ring (chemistry) , pyridine , hydrate , moiety , hydrazine (antidepressant) , nucleophile , fragmentation (computing) , pyrimidine , nitrogen atom , medicinal chemistry , stereochemistry , organic chemistry , catalysis , chromatography , computer science , operating system
Heating of 5‐nitropyrimidine with acetic acid in water leads to the formation of 3,5‐dinitro‐pyridine. The mechanism proposed for this novel ring transformation involves a fragmentation of the pyrimidine ring, leading to the formation of a two ‐atom and a four ‐atom moiety, which on condensation gives the pyridine ring. With hydrazine hydrate, 5‐nitropyrimidine undergoes ring contraction into 4‐nitropyrazole.